Photoinitiated by red light (625 nm) iodosulfonylation of internal alkynes to synthesize β-iodovinylsulfones
- 作者: Abramov V.A.1, Topchiy M.A.1, Malysheva A.S.1, Beletskaya I.P.1, Asachenko A.F.1
-
隶属关系:
- Topchiev Institiute of Petrochemical Synthesis, Russian Academy of Sciences
- 期: 卷 59, 编号 12 (2023)
- 页面: 1620-1625
- 栏目: Articles
- URL: https://archivog.com/0514-7492/article/view/667155
- DOI: https://doi.org/10.31857/S0514749223120066
- EDN: https://elibrary.ru/OENHJV
- ID: 667155
如何引用文章
详细
Synthesis of β-iodovinyl sulfones was performed out by direct bifunctionalization of internal alkynes using an economical LED light source with a maximum emission wavelength of 625 nm. The products were obtained in high yields (68 to 99%) using equivalent amounts of reagents. The reaction of arylsulfonyl iodides with internal alkynes proceeds by a radical mechanism and is a regioselective method for the synthesis of β-iodovinyl sulfones.
作者简介
V. Abramov
Topchiev Institiute of Petrochemical Synthesis, Russian Academy of Sciences
M. Topchiy
Topchiev Institiute of Petrochemical Synthesis, Russian Academy of Sciences
A. Malysheva
Topchiev Institiute of Petrochemical Synthesis, Russian Academy of Sciences
I. Beletskaya
Topchiev Institiute of Petrochemical Synthesis, Russian Academy of Sciences
A. Asachenko
Topchiev Institiute of Petrochemical Synthesis, Russian Academy of Sciences
Email: aasachenko@ips.ac.ru
参考
- Beletskaya I.P., Ananikov V.P. Chem. Rev. 2011, 111, 1596-1636. doi: 10.1021/cr100347k
- Beletskaya I.P., Ananikov V.P. Chem. Rev. 2022, 122, 16110-16293. doi: 10.1021/acs.chemrev.1c00836
- Tatevosyan S.S., Kotovshchikov Y.N., Latyshev G.V., Erzunov D.A., Sokolova D.V., Beletskaya I.P., Lukashev N.V. J. Org. Chem. 2020, 85, 7863-7876. doi: 10.1021/acs.joc.0c00520
- Gevondian A.G., Kotovshchikov Y.N., Latyshev G.V, Lukashev N.V., Beletskaya I.P. J. Org. Chem. 2021, 86, 5639-5650. doi: 10.1021/acs.joc.1c00115
- Burykina J.V., Kobelev A.D., Shlapakov N.S., Kostyukovich A.Y., Fakhrutdinov A.N., K�nig B., Ananikov V.P. Angew. Chem., Int. Ed. 2022, 61, e202116888. doi: 10.1002/anie.202116888
- Scott K.A., Njardarson J.T. Top. Curr. Chem. 2018, 376, 5. doi: 10.1007/s41061-018-0184-5
- Reddy R.J., Kumari A.H. RSC Adv. 2021, 11, 9130-9221. doi: 10.1039/D0RA09759D
- Padma Priya V.R., Natarajan K., Nandi G.C. Tetrahedron. 2022, 111, 132711. doi: 10.1016/j.tet.2022.132711
- Dong B., Shen J., Xie L.-G. Org. Chem. Front. 2023, 10, 1322-1345. doi: 10.1039/D2QO01699K
- Reddy R.J., Kumar J.J., Kumari A.H., Krishna G.R. Adv. Synth. Catal. 2020, 362, 1317-1322. doi: 10.1002/adsc.201901550
- Reddy R.J., Kumar J.J., Kumari A.H. Eur. J. Org. Chem. 2019, 2019, 3771-3775. doi: 10.1002/ejoc.201900676
- Reddy R.J., Kumari A.H., Sharadha N., Krishna G.R. J. Org. Chem. 2022, 87, 3934-3951. doi: 10.1021/acs.joc.1c02444
- Reddy R.J., Sharadha N., Krishna G.R. J. Org. Chem. 2023, 88, 8889-8903. doi: 10.1021/acs.joc.3c00671
- Fang Y., Luo Z., Xu X. RSC Adv. 2016, 6, 59661-59676. doi: 10.1039/C6RA10731A
- Li X.-Q., Liao Q.-Q., Lai J., Liao Y.-Y. Front. Chem. 2023, 11, 1267223. doi: 10.3389/fchem.2023.1267223
- Mulina O.M., Ilovaisky A.I., Parshin V.D., Terent'ev A.O. Adv. Synth. Catal. 2020, 362, 4579-4654. doi: 10.1002/adsc.202000708
- Kumar S., Kumar J., Naqvi T., Raheem S., Rizvi M.A., Shah B.A. ChemPhotoChem. 2022, 6, e202200110. doi: 10.1002/cptc.202200110
- Kumar R., Dwivedi V., Sridhar Reddy M. Adv. Synth. Catal. 2017, 359, 2847-2856. doi: 10.1002/adsc.201700576
- Gurawa A., Kumar N., Kashyap S. Org. Chem. Front. 2023, 10, 4918-4926. doi: 10.1039/D3QO01188G
- Tong C., Gan B., Yan Y., Xie Y.-Y. Synth. Commun. 2017, 47, 1927-1933. doi: 10.1080/00397911.2017.1337152
- Truce W.E., Wolf G.C. J. Org. Chem. 1971, 36, 1727-1732. doi: 10.1021/jo00812a001
- Abramov V.A., Topchiy M.A., Rasskazova M.A., Drokin E.A., Sterligov G.K., Shurupova O.V., Malysheva A.S., Rzhevskiy S.A., Beletskaya I.P., Asachenko A.F. Org. Biomol. Chem. 2023, 21, 3844-3849. doi: 10.1039/D3OB00437F
- Cao L., Luo S.-H., Jiang K., Hao Z.-F., Wang B.-W, Pang C.-M., Wang Z.-Y. Org. Lett. 2018, 20, 4754-4758. doi: 10.1021/acs.orglett.8b01808
- Peng C., Gu F., Lin X., Ding N., Zhan Q., Cao P., Cao T. Green Chem. 2023, 25, 671-677. doi: 10.1039/D2GC04296G
- Ma Y., Wang K., Zhang D., Sun P. Adv. Synth. Catal. 2019, 361, 597-602. doi: 10.1002/adsc.201801258
补充文件
